Trityl chloride → HCID 86651441, compound

Participants

Reaction Steps

To a solution of 1-(2-deoxy-β-D-ribofuranosyl)-4-(1-propynyl)pyrrole-2-carbaldehyde (249 mg, 1.00 mmol) (I. Hirao, et al., Nature Methods, 3: 729-735 (2006)) dissolved in anhydrous pyridine (10 ml) were added trityl chloride (1.18 g, 4.21 mmol) and N,N-diisopropylamine (1.11 ml, 6.40 mmol), and the reaction mixture was stirred at room temperature for 29 hours, and then at 50° C. for 1.5 hours. The reaction solution was concentrated under reduced pressure, and the residue was diluted with ethyl acetate, and the organic layers were washed twice with a saturated aqueous sodium bicarbonate solution and dried over magnesium sulfate. The resulting crude product was purified by column chromatography on silica gel (eluent:dichloromethane:ethyl acetate=100:0→400:3, then dichloromethane:methanol=100:2) to give the title product (395 mg, 80%).

Provenance & Evidence